Access to Fully Substituted Thiazoles and 2,3-Dihydrothiazoles via Copper-Catalyzed [4 + 1] Heterocyclization of α-(<i>N</i>-Hydroxy/aryl)imino-β-oxodithioesters with α-Diazocarbonyls

Srivastava, Abhijeet; Shukla, Geeta; Yadav, Dhananjay; Singh, Maya Shankar

doi:10.1021/acs.joc.7b01601

Cited by 30 publications

(11 citation statements)

References 97 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…An interesting procedure for the chemoselective synthesis of 2,4,5-substituted thiazoles from diazo carbonyls 129 and α -( N -hydroxy/aryl)imino- β -oxodithioesters 130 / 132 was reported in 2017 by Srivastava and co-workers [ 68 ]. The [Cu(CH 3 CN) 4 ]PF 6 -catalyzed reaction gives access to both 5-mercaptothiazoles 131 and 5-mercapto-2,3-dihydrothiazoles 133 in good to excellent yields.…”

Section: Azoles With Two Heteroatomsmentioning

confidence: 99%

Diazocarbonyl and Related Compounds in the Synthesis of Azoles

et al. 2021

View full text Add to dashboard Cite

Diazocarbonyl compounds have found numerous applications in many areas of chemistry. Among the most developed fields of diazo chemistry is the preparation of azoles from diazo compounds. This approach represents a useful alternative to more conventional methods of the synthesis of azoles. A comprehensive review on the preparation of various azoles (oxazoles, thiazoles, imidazoles, pyrazoles, triazoles, and tetrazoles) from diazocarbonyl and related compounds is presented for the first time along with discussion of advantages and disadvantages of «diazo» approaches to azoles.

show abstract

Section: Azoles With Two Heteroatomsmentioning

confidence: 99%

Diazocarbonyl and Related Compounds in the Synthesis of Azoles

et al. 2021

View full text Add to dashboard Cite

show abstract

“…Srivastava group developed a chemoselective method for preparing tri‐substituted thiazoles ( 294 ) using imino‐ β ‐oxodithioesters ( 292 ) and diazo carbonyls ( 293 ). This protocol resulted in the formation of 2,3‐dihydro thiazoles ( 295 ) as a competitive by‐product.…”

Section: Synthesis Of Thiazolesmentioning

confidence: 99%

An Overview of Recent Developments in the Synthesis of Substituted Thiazoles

et al. 2020

View full text Add to dashboard Cite

Thiazole frame work represents a vital pharmacophore in several areas of chemistry. Consequently, several synthetic protocols to construct and functionalize this core, in an attempt to generate diverse thiazole containing architectures have been developed by various researchers across the globe. These wide range of methodologies developed will allow the access to fully decorated thiazole containing new chemical entities that can find various application in the field of medicinal chemistry, agrochemicals and material science. This review will provide an insight in to the various synthons used in construction and diversification of this core. Diversely functionalized thiazole analogs are considered as a vital azole framework present in many natural products. This prominent heterocycle also constitutes an important pharmacophore in medicinal chemistry, in agrochemicals and in molecules for material science applications. All these above‐mentioned features of thiazole necessitates the continuous development of efficient methods to access this heterocycle. Accordingly, various researchers across the globe have come up with efficient synthetic protocols in an attempt functionalize different positions of this important scaffold. This review aims at highlighting some of the latest synthetic approaches to di/tri‐substituted thiazole analogs which are known to possess a wide spectrum of biological activities.

show abstract

“…Also, the thiazole nucleus is present in a large number of drugs like antibiotics (penicillin, cephalosporin, and micrococcin), Abafungin and Ravuconazole as antifungal drugs, Ritonavir as an anti-HIV drug, and Sulfathiazole as an antimicrobial drug [11]. Several methods for the synthesis of thiazoles and their derivatives were developed by various catalysts, conditions, and strategies [12][13][14][15][16][17][18][19][20][21]. From these methods, we were interested in the synthesis of thiazoles by condensation of α-halo ketones with thioamides [22][23][24][25][26][27][28].…”

Section: Introductionmentioning

confidence: 99%